Just finished reading this entire thread.
I just booked a last minute flight to Italy over Thanksgiving. I'm flying out on Sunday the 20th to Florence and will return on Nov 30th, but my return flight isn't booked yet.
All I have booked so far for accommodations is 3 nights in Florence and then one night in Siena. I have a rental car booked to drive from Florence to Siena and then was going to continue down to Naples/Sorrento/Salerno area, drop the car off in Naples and fly home from there.
After reading through the thread I think I may scratch driving down to the Naples area, spend another night in Siena, and spend more time in Tuscany. Driving around the countryside hitting up wineries and restaurants in small villages sounds appealing to me. I could then fly back from Florence.
A few questions to the Surly Italian Mafia:
Should I skip picking up the car in Florence and just take the train/bus to Siena and get a car there? Sounds like driving in Florence kind of sucks and the rental car place I'm booked at is in downtown Florence.
Are any of the coastal cities around the Tuscany area worth driving to and visiting? Any other recommendations for things to do in the Tuscany area?
Any specific recommendations for an Agriturismo to stay at in Tuscany? Should I just book one as a base and then day trip to other villages/wineries or should I stay at different ones?
For context, I went to Italy once back in 2012, but only visited Rome. I spent 5-6 days there, so don't feel the need to go back on this trip.